Annie Hellish
by minaviolet44
Summary: Starts after 10x5. Sam knew Dean had tortured in Hell. But it'd always been an abstract thing, until tangible proof walked up to them and shoved it in their face.
1. One

Sam would say that killing a monster pretending to be Paris Hilton was the weirdest hunt he'd ever been on, but then he would be lying.

Right now, he and Dean aren't on a hunt—Dean is actually at a homemade pie bakery, citing it's one of the best he's ever been to (Sam assumes it was probably from when he was at Stanford, because he doesn't recognize the place)—and Sam is outside, sitting on a wooden bench.

"Sammy!" He hears Dean call. Sam turns to see Dean holding up a bag emitting the strong smell of pecans and apples. Dean grins.

"Pie!" He exclaims happily, like a little kid, and Sam smiles. In the wake of the apocalypse, Dean had begun to stop smiling like that—Sam made sure to remember the small moments when he did. He wondered if he should try to make more of an effort to remember to buy pie for Dean.

At least now Dean wasn't acting as if Sam was the bane of his existence. Sam blamed himself for the apocalypse—because _he_ had been the one who'd killed Lilith, no one else—and he _knew_ it was his fault. He didn't need Dean to remind him.

Sam knew he'd probably never get back Dean's trust completely, after the demon blood, but he could try. He _would_ try.

Who could he depend on, if not his older brother?


	2. Two

They don't go to the car immediately. Dean sits down on the picnic bench, and opens up one of the pie boxes, ready to start stuffing himself, when they're interrupted by a girl's voice.

"Hey, you're the Winchesters, right?" Sam and Dean both look up sharply, Sam's hand flying to the demon knife, Dean…protectively hovering over his pie? Sam gives his brother a bitch face, and Dean looks a little sheepish.

"Who's asking," Sam says. The girl grins—she's a ginger, green-eyed, about sixteen. Her clothes are those you'd see on a street kid.

"I'm Annie," she says, "and I'm a demon." Her eyes flick black, then, and Sam's hand closes around the handle of the knife and Dean has long put down his pie. Why did every moment of peace have to be ruined by something like this?

"Whoa," she raises her hands. "I'm not here to like, kill you or anything. I'm on your side."

Dean snorts, and Sam's eyes narrow. "Like Ruby was on our side?" Dean sneers.

"Uh, Hell no." She giggles. "Ooh, punny. But seriously, no. She was _such_ a skank. I would never try to seduce Sam Winchester."

Sam and Dean just stare at her. What kind of demon is this?

"Every girl you sleep with dies," she says after that, and Sam can't help but wince, just a little.

"Not all of them," he protests, and Dean just glares.

"Look, this is fun and all, but the hell do you want with us?" He growls. The demon sighs.

"You really forgot me, Dean—I mean, _Dad_? Hello, I'd've thought you'd remember your kids—you remembered Alastair, after all."

Sam's confused, but Dean's face goes through an interesting series of expressions—first confusion, then pale horror and ashen comprehension, and finally settles on bone white.

"Dean?" Sam asks tentatively.

"Lily-Anne James," Dean chokes out.

The girl smiles like a Cheshire cat. "Bingo!" She claps.


	3. Three

Sam has no idea what's going on, other than that it has something to do with the time Dean spent in Hell.

"Dean, what's going on?" He asks in a low voice. Dean turns to look at him—Sam hasn't seen his eyes so haunted since back when he first got dragged out of Hell.

"Meg called Alastair 'Dad', Sammy," he says. "Connect the dots."

Sam blinks and thinks. He reaches a conclusion in seconds. Meg had called Alastair 'Father' because he had been the one to torture her and indoctrinate her into torture. The demon—Lily-Anne, Annie—called Dean 'Dad'.

Dean had tortured for ten of his Hell years.

"Oh," Sam says. It's all he can say, really. The demon—Annie—lifts a brow.

"So, Dad, I'm on your side," she says. "Because Lucifer is overrated and I heard on the grapevine the demons sucking up to him are dropping like flies."

Sam blinks at that unexpected piece of info. Before he can question it, she waves a hand at him.

"He keeps using them for sacrificial spells," she explains. Dean just continues to stare at her in shock.

"Oi, Dad, I followed you out of Hell, and I can be an informant for you," she complains. "Aren't I gonna get a thanks."

"You were sixteen," Dean says suddenly. "You made a deal because you wanted your Dad to stop hurting you, when you were five."

Sam stares at them both. He'd almost forgotten—demons they might be now, but they had once been human too.

"I told you I'd be your new Dad," Dean continues. "You broke in a month."

"You were sixteen," he repeats, like a broken record. Sam knows he can't even begin to understand the crushing guilt Dean probably feels right now.

"Calm down," Annie says. "You were a better Dad then mine, 'ey? 'Least you didn't rape me," she grumbles.

Dean looks like he's about to be sick, and Sam feels the same.

The pie lays forgotten on the bench.


	4. Four

Sam clears his throat, then speaks.

"So…you're saying you're on our side because Dean _tortured_ you?" He can't help the incredulous tone that enters his voice. How exactly was he supposed to take that? Wasn't this some sort of twisted…Stockholm syndrome type situation? But did it count if she was a demon?

And what if she was just another Ruby?

Annie looks irritated at the question. " _No_ ," she says. "I'm on your side because Dean taught _me_ how to torture."

Dean's expression becomes even more horrified at that—but not with shock, Sam thinks. More with realization of something he's tried extremely hard to forget. Sam can relate—on the trying to forget part.

He hasn't quite caught up with the 'my brother taught a teenage girl how to torture' part. He probably won't ever wrap his head around that.

"He's the reason I became a demon," she continues. "So, since my human dad was shitty anyway, Dean's my dad."

 _He's the reason I became a demon._ Sam stares at Dean, trying to gauge his reaction to that. Dean still hasn't spoken a single word. In fact, Sam thinks he might be going into shock. Forty years of Hell could definitely give a guy PTSD, and Sam knew Dean had panic attacks and tried to pass it off as normal when Sam asked about it.

Sam pauses in his rambling trail of thought, and wonders if he's in shock too, though maybe not to the point Dean is.

"Hey, Dad, you alright?" Annie asks, and a part of Sam laughs at the incredulity of it all. A demon, calling Dean 'Dad', and asking him if he was alright. And Sam thought _he_ was the one with demon issues.

"Don't," Dean finally says, and Sam attempts to pull himself back into reality.

 _You call this reality?_ Internal Dean says.

"Don't what, Dad?" Annie asks in confusion. Dean's head snaps up, and he finally looks Annie in the face, really looking at her, not just staring at some horrific memory of Hell.

"Don't call me that. I'm not your Dad. I tortured you. I made you torture. I'm not your Dad—"

"I'm not the crying girl I was when you first got me," Annie interrupts him. "I'm a _demon_ , and as a demon, my father is you, and my loyalty is to you. You were probably the only good soul in Hell that was assigned to my rack, and you're the reason I'm still coherent, even as a demon that's only a few Hell-decades old."

 _Hell-decades_. Dean tortured for years, in Hell, and Sam sometimes forgets that times passes differently down there—it was only four months for him. The worst four months of his life, yes, but still only four months. Not four decades.

Dean had been down there for that long, and this once-girl for even longer. He knew being tortured had been hard for Dean, even as a seasoned and experienced hunter—he can't imagine what it would've been like for an abused teenage girl.

He doesn't want to imagine.


	5. Five

Sam definitely does not want to drive around with a demon in the backseat. That said, apparently, Dean isn't as worried.

Sam thinks his judgement might be a bit impaired by the fact that he was the one who turned the girl into a demon into the first place. Not that Sam has any right to judge—hello, Ruby. It's because of this that Sam doesn't say anything.

The inside of the car is filled with an extremely awkward air. Nobody is talking—Dean is driving with short, jerky motions, not at all his usual smooth self, Sam himself just sits straight and isn't looking at Dean or Annie, and Annie…

Annie is humming. What the hell?

Sam glances at the rearview mirror. Her lips are moving—she is humming. The song seems familiar too—like something Dean would like. Annie notices Sam's eyes reflected at her in the mirror and gives a little wave. Sam looks away.

She has Dean's music taste. Really, the way she acts, Sam could almost forget she was a demon in the first place.

She wasn't like Ruby at all. With Ruby, Sam had been jarringly aware she was a demon—though her words had shown she was ashamed of her demonhood, her actions had shown pride in it. She held herself high, mockingly called him racist when he brought it up.

And of course, there had been the moment after Sam had killed Lilith. It was the most obvious then—she had never really hated being a demon—she had been worshipful of Lucifer like every other demon. Sam had looked back on that moment and wondered how he'd been so blind—what exactly had he gone to Stanford for, again?

Annie, on the other hand, doesn't even seem to notice she _is_ a demon. She plays with her hair—not hers, Sam reminds himself, her meatsuit's—she taps her finger to some beat only known to her on her knee. She has a pink purse—a cellphone in her pocket. She doesn't seem to care, either way, demon or human.

Sam is pulled away from his thoughts when Dean speaks up.

"Who's the meatsuit?" He says, in a gruff voice.

Annie stops twirling her hair and meets his eyes through the mirror.

"My comatose twin sister," she says, smirking. Sam blinks in surprise. Comatose meatsuit? Wait, back up. _Twin sister?_

"W-what?" Dean actually stutters. Sam doesn't blame him.

Annie rolls her _meatsuit's_ eyes. "Hello, I was human? And I didn't die _that_ long ago. My dad put my sister in a coma about a week before I died—I'd already sold my soul, so I couldn't deal twice. Pretty sure her soul's already in Heaven anyway."

Sam can't even get shocked anymore. He actually finds himself wondering if they can really trust Annie.

But Ruby, his mind all but screams. But Ruby had never spoken of her family, had she? She probably hadn't even remembered them—Sam had remembered her saying that she was a witch when she was human. She'd thought of Lucifer as her God and other demons as competition.

Maybe all demons _aren't_ pro-Lucifer.


	6. Six

"Hey, Dean," Sam says, looking up from his laptop. He's sitting in the Impala, looking through cases on his laptop. A particularly odd one has caught his eye. He gets no response, and looks up—the driver's door is open, the seat empty.

The car is parked, next to a deli—go figure, Dean has probably left to get his beloved pie. Sam rolls his eyes, outwardly, but winces on the inside. It isn't like he _means_ to forget the pie—he just…doesn't remember.

And Dean kind of needs it right now, Sam supposes, after discovering a demon he tortured considers itself his daughter. Speaking of which…

Sam turns to the backseat. Annie is on her phone, tapping away. Sam wonders what exactly she's even doing on it.

Annie looks up, and waves her fingers in a mocking hello.

"Jailbait, Uncle Sam," she drawls, and Sam frowns.

"What are you doing on that phone, anyway," Sam asks, with not wariness in his voice (like there should be), but instead just plain curiosity.

"Updating my Facebook status," she answers. Sam's eyebrow's raise.

"You have a Facebook?"

"Of course," she answers. "Just because all the other demons are stuck in the 8s doesn't mean I'm not keeping up with current trends. I mean, just _look_ at Ruby. Black leather? _So_ cliché. Ugh." Annie waves her hand in a sort of disgusted motion.

Sam has no idea how to react to that. He's actually honestly trying not to snort. Ruby _did_ wear a lot of black leather…

Okay, now is really not the time for funny banter. Sam looks longingly at the deli. He wishes Dean would come back sooner. He doesn't know how to deal with children—that's always been Dean's thing.

Annie is looking at him with her head tilted. "Hey, Uncle Sam," she says, and he really wishes she wouldn't call him that.

"Weren't you addicted to demon blood or something? Why aren't you trying to jump my bones?"

Sam does not want to talk about this. Not right now. It's still way too soon.

"Not anymore," is all he says, and Annie doesn't ask any more about the topic. Sam has a question of his own.

"Why do demons call the one who tortured and turned them their parent?"

Annie looks surprised. "Oh, that's part of the process," she answers. "See, while we're getting tortured, we slowly loose the human memories we have, When we turn, they come back, but we don't really _feel_ anything about them anymore—our human selves aren't really _us_ anymore. Most demons actually take up a new name—me, I call myself Annie because it's funny. Hi, I'm Annie, the evil demon."

She says it with great amusement, but rolls her eyes and continues her explanation when Sam gives no reaction.

"Our souls don't start the corruption process until we begin to torture, and it works faster on the weaker souls, like me. When it's complete, we turn. In all honesty, our torturer is literally our parent—a small, miniscule really, part of their soul is gone when they turn someone, completely corrupted. It goes to the newborn demon."

Sam digests this information, and reels in shock. "You have a piece of Dean's _soul_ in you?"

"Yeah. It's how I tracked him. Don't worry," she says, misinterpreting the panic on Sam's face. "I'm the only one he turned fully, no other demon can track him like me."

But Sam isn't at all worried about _that_.

Dean is _missing a part of his soul._ How—what does that mean? For him? For Annie? Dean is still Dean, but how can Sam know for sure? Sure, the _angels_ had brought him back, but now he knew the angels were dicks.

Surely Cas would have brought him back properly, though, right?

Of course Dean chooses that exact moment to come back to the car. Sam turns to him, all information about the hunt forgotten in light of Annie's reveal.


End file.
